Water → HCID 178419282, compound

HRID 1775025Notes

Reaction equation

HRID 1775025 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[N:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:5]2=[CH:6][N:7]=1.[NH:18]1[CH:22]=[CH:21][C:20](B(O)O)=[N:19]1.C([O-])(=O)C.[K+].O>C(=O)([O-])[O-].[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:22]3[CH:21]=[CH:20][NH:19][N:18]=3)=[N:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:5]2=[CH:6][N:7]=1

Participants

8

Reactant 4

HCID 962Water2×HCID 517044Potassium AcetateHCID 726984825-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridineHCID 178514837HCID 178514837, compound2×

Product 1

HCID 178419282HCID 178419282, compoundYield 44.1%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

A microwave reaction vial was charged with 5-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine (408.03 mg, 1.0 mmol), 1H-pyrazol-3-ylboronic acid (117.49 mg, 1.05 mmol), 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (81.66 mg, 0.1 mmol), 1.00 M of Potassium acetate in Water (1.5 mL, 1.5 mmol), 1.00 M of Sodium carbonate in Water (1.5 mL, 1.5 mmol), and Acetonitrile (3 mL). The reaction mixture was heated under microwave at 100° C. for 20 minutes. Added another 2 equivalents of 1H-pyrazol-3-ylboronic acid and continue heated under microwave at 100° C. for 20 minutes. The same procedure was repeated 2 more times. The mixture was concentrated and the residue was purified on silica eluted with 0 to 100% Ethyl acetate in Heptane to afford 5-bromo-3-(1H-pyrazol-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine as an off-white solid (153.7 mg, 44%).

Workup

  1. customA microwave reaction
  2. temperaturecontinue heated under microwave at 100° C. for 20 minutes
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified on silica
  5. washeluted with 0 to 100% Ethyl acetate in Heptane

Sources & evidence

ORD record
ord-b32d57ba15024626bf3cf06572564068
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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